Why the Chicago Mac is America’s Greatest Sailing Regatta

Jul 30th 2018

Farr 40 sailor Jill Mecklenburger says every sailor should
do at least one Mac—and then you’ll keep coming back for more.

A few days before the Chicago Yacht Club’s 2018 Race to Mackinac, we got a request from audiologist and Farr 40
Eagles
Wings
sailor Jill Mecklenburger. With the forecast growing increasingly
menacing (25 – 30 knots of breeze from the north with ocean-sized swells), she
needed
a
pair of boots up to the challenge.

Jill grew up cruising Lake Michigan with her family but didn’t
start racing until the 2000 Chicago Mac, thanks to an invite from her
then-boyfriend who had recently purchased a Nelson Marek 41. The boyfriend is
long gone, but Jill fell in love with the Mac. She’s since raced six on a
C&C 42, a Corsair 31 trimaran, seven on the TP52
Imedi (Jon Santarelli, the Imedi sailor who tragically went overboard at the start of the 2018 race, was a friend), and now Eagles Wings.

The Chicago Mac was voted the “Greatest American Sailing Regatta” in a March Madness-style tournament bracket created by U.S. Sailing. We
learned the 110th annual race would be Jill’s 19th (it
would be the fourth for this writer) and we got to thinking—what is it about
this regatta that keeps sailors coming back, year after year after year?

The competition

There’s no doubt that one of the most appealing aspects of
the Mac race is the competition. The monohull race record of 23 hours, 30
minutes, and 34 seconds was set by Roy E. Disney’s
Pyewacket in 2002. The 100th race held in 2008 drew more
than 400 boats. Most years the Chicago Mac hosts an average of 300 boats crewed
by some 3,000 sailors. The
Island Goat Sailing Society was established in 1959 for sailors who had completed at
least 25 Mac races—the current roster has over 370 members!

Farr 40 sailor Jill Mecklenburger only needs six more Macs to be invited to join the Island Goat Sailing Society.

The race attracts the crème de la crème of professional
sailors, including Volvo Ocean, America’s Cup, and Sydney to Hobart veterans,
as well as numerous Olympic champions and medalists. The pros compete alongside
the amateurs in three divisions and about 30 sections in boats as small as the
Tartan 10, up to Doug DeVos’s 86-foot
Windquest.

“To race the Mac, you have to be an accomplished sailor, you
have to know what you’re doing. It’s the highlight every summer for all the
sailors in Chicago and all the people who come here, too,” said Jill.

You never know what you’re going to get

While race conditions are predominantly governed by currents
and prevailing winds in the ocean, in Lake Michigan, weather rules the water, which
means you never know what you’re going to get and conditions often turn on a
dime. On any given weekend in July, “Michi-gami”—Ojibwe for “great water”—
could serve up shorts and t-shirts downwind all the way, it could be as calm as
a millpond, or gale force winds could produce 10 – 12-foot swells. But the
unpredictable weather is part of the race’s allure.

“2018 was one of the roughest Macs in terms of conditions.
It was like last year, but much, much worse. I’ve never done a Mac when we never
put up the spinnaker,” said Jill. Her advice for first-time Mac racers: “Be prepared for anything. It can be beautiful champagne sailing, or it can be
really rough, but that's the fun of it I think.”

Farr 40 Eagles Wings prepares to take flight.

Course geography and tactics

The 289-nautical mile course is the longest freshwater
course in the world. It starts off Navy Pier in Chicago and finishes at
Mackinac Island, with only four designated marks along the way: three buoys and
the Mackinac Bridge. But there are a number of tactical decisions to be made.
Depending on the weather, a boat may hug the Wisconsin shore off the start
line, or head immediately for Michigan. Other years, the fastest route may be
right up the middle.

Native American legends describe the origin of many of the
geographical features along the course, including the Manitou Islands and
Sleeping Bear Sand Dunes. The New Shoal Lighted Bell Buoy marks the rounding
into the Straits of Mackinac and holds it’s own lore for sailors. “It’s kind of
a famous place where people will drop ashes of sailors as they round the mark
or they’ll have a drink for somebody,” Jill explained.

There are also currents to consider through the Straits, the
connecting body of water between Lake Michigan and Lake Huron, which change
direction about every 36 hours.

“It can be so challenging, but you feel such a sense of
accomplishment once it’s done. I think if it were easy, it wouldn’t be as much
fun,” said Jill.

The magic of Mackinac

If you’ve never done a Mac—and Jill is adamant that every
sailor should do at least one—you’ve never experienced the singular feeling of
arriving on Mackinac Island by sailboat, stepping on the dock and back in time,
to a place where bicycles and horse-drawn carriages rule, colonial dress
(inside Fort Mackinac) is de rigueur, and the Michilimackinac courthouse and
police station have been functioning non-stop since 1839. Oh, and if that's not enough, every boat gets a "cannonball" salute as they cross the finishing line.

“It’s such a magical place. Some people think it’s
too touristy, but I just love everything about it,” said Jill.

The crew bus heads back to Chicago on Wednesday, but it’s
well worth your while to book a few extra days on the island. Stay at the
historic Grand Hotel, enjoy a round of golf against the backdrop of turquoise
blue water, dine on fresh whitefish or splurge on a pound of housemade fudge, pack
a lunch and ride a tandem bike around the ring road, or take a hike up to Skull
Cave, so named for the number of human bones found inside.

Sailboats docked at Mackinac Island with historic Fort Mackinac on the hill in the distance.

The social scene

It’s been said that the Chicago Mac is the unfortunate part
between two great parties. While that may be more or less true depending on the
year, the Chicago Yacht Club and the residents of Mackinac Island work hard to
create a welcoming and celebratory atmosphere on both ends. The weekend starts
with the Warning Gun Party in Chicago and finishes with the Sailors’
Celebration on the Island. And then there’s The Pink Pony.

The iconic bar with the patio full of pink umbrellas is
conveniently located in the Chippewa Hotel, a short stumble from the municipal
docks. “The Pony” has been the site of the unofficial sailors’ party since it
opened in 1948. Order a Rum Runner and head out to the hot tub to enjoy the
live music and associated mayhem.

Regardless of the ride, if it’s a slog one year, it will be
wonderful the next. As one 35-year veteran said, “When things get rough on this
race, just close your eyes and remember all the good ones.”